Normal secondary tridecyl sulphates



Patented June 17, 1947 NORMAL SECONDARY TRIDECYL SULPI-IATES Emil E. Dreger, Summit, and John Ross, Ramse N. J assignors to Colgate-Palmolive-Peet Company, Jersey City, N. J a corporation of Delaware No Drawing. Original application July 9, 1937,

Serial No. 152,852. Divided and this application February 19, 1943, Serial No. 476,466

4 Claims.

This invention relates to new materials adapted to function as wetting agents, detergents or the like. More particularly, the invention relates to the utilization of short chain fatty acids, which are not ordinarily satisfactory for the preparation of detergents, wetting agents, and the like, for the production of materials which will function emciently for these purposes.

The fatty oils that are commonly used in the production of detergent materials almost invariably contain an appreciable percentage of fatty acid esters, the fatty acids of which contain less than 12 carbon atoms. The sodium salts of these fatty acids are of little or no value and, if they are left in the mixture along with the salts of the higher fatty acids, the result is simply a corresponding amount of inactive or inemcient material in the final product. This fact has been recognized and in some instances these lower fatty acids have been removed to make the final product more effective. The removal of such fatty acids, however, reduces the quantity of the final detergent product that can be produced from a given amount of fatty oil and yields, as a lay-product, considerable quantities of these lower fatty acids. For example, about 21% of the fattyacids in cocoanut oil contains less than 12 carbon atoms, and about 13% of the acids in palm kernel oil also contains less than 12 carbon atoms.

According to the present process, these fatty acids, containing more than 1 and less than 12 carbon atoms and which are almost entirely of the straight chain or normal variety, are reacted in such a way as to form useful, efficient detergents, wetting agents, or the like. Preferably, the fatty acids that are used according to the present process are straight chain fatty acids and have at least 6 and not over 11 carbon atoms.

Briefly, the process of the present invention is acomplished by converting the fatty acids into co-pending application Serial No. 152,852, filed July 9, 1937, now Patent No. 2,321,020, granted June 8, 1943, of which the present application is a division.

The process of the present invention was applied to caproic acid, caprylic acid and capric acid as well as to mixtures of caprlc' and caprylic acids and of all three acids. The individual acids yielded di-n-amyl carbinol sulphate salt, di-nheptyl carbinol sulphate salt, and di-n-nonyl carbinol sulphate salt respectively. The mixture of caprylic and capric acid gave a mixture of di-n-nonyl carbinol sulphate salt, di-n-heptyl carbinol sulphate salt and n-heptyl n-nonyl carbinoi sulphate salt. The mixture of all three acids produced in addition to the others n-amyl n-heptyl carhinol sulphate salt and n-amyl n-noyl carbinol sulphate salt.

The relative wetting and foaming properties of solutions of some of the compounds are compared below, showing the outstanding and unusual emciency of di-n-heptyl c'arbinol sulphate sodium salt in these respects.

Foam, cc. Wetting Time Material 05% in Hard Water 1.0 0.25 500 P. P. M

Di-n-lieptyl carbine] sul hate sodium salt Cu sxOSOaNa n-hep l n-nonyl carblno sul hate sodium Still: 01'! uOSO3NB.

Di-n-nonyl carbinol sul hate sodium salt C10 aOSOaNa Mixed sodium salts of carbinol sulphates from m es 0! Ca, C5, C10 acids a. one inch square of unused canvas drill. By' placing cc. of the solution to be tested in a.

beaker, the time required to wet the square of cloth dropped upon the surface of the solution can be readily measured with a stop watch. In most cases the cloth will sink to the bottom as soon as it is thoroughly wet.

Generally the secondary alcohol sulphates prepared by the process should contain at least 11 carbon atoms to be satisfactory as emulsifying and deterglng agents. That is, if a single acid is used to prepare the secondary alcohol it should contain at least 6 carbon atoms and, if a mixture of acids is used, the sum of the carbons in their chains should be at least equal to 12 carbon atoms. For example, n-butyric acid (4) and n-caprylic acid (8) will yield along with other sulphates, n-propyl n-heptyl carbinol sulphate salt which has 11 carbon atoms in the compound.

Although the preferred compounds are prepared from the straight chain fatty acids containing not less than 6 and not more than 11 carbon atoms, the process is adapted to the use of any straight or branch chain aliphatic monocarboxylic acids other than formic acid. i. e., acetic acid and its higher homologues, whether derived from fatty oils or from any other source, such as the oxidation of petroleum, alcohols and aldehydes, de-esteriflcation of oils, fats and waxes and by organic synthesis.

Mixtures of lauric and n-butyric and of lauric and isobutyric acids were converted into ketones and the pure n-propyl undecyl ketone and isopropyl undecyl ketone obtained by fractionation. These were reduced to the respective carbinols which were converted into acidsulphates and neutralized.

The following comparison of the wetting and foaming properties of these two isomeric compounds discloses the marked superiority of the straight chain compound as a wetting agent.

Foam, 00. @33

Material 9 1 Hunt 1 025 soonr.

Iso ropyl undeoyl carbinol sulgate sodium salt OuHn BO'Na 326 115 13 73 n-propyl undecyl carbinol sulphate sodium salt OuHn OBOINa 300 100 2 22 The present invention is not to be restricted to any specific proportionswr manner of procedure beyond the limitation of the appended claims.

We claim:

1. A normal, secondary, tridecyl sulphate.

2. N-amyl n-heptyl carblnol sulphate.

3. Normal sodium tridecyl-6 sulphate.

4. A salt of a normal, secondary, tridecyl sulphate.

EMIL E. DREGER. JOHN ROSS.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,027,896 Bertsch Jan, 14, 1936 2,229,649 Guenther et a1. Jan. 28, 1941 2,088,018 Wickert et al. July 27, 1937 2,108,133 McCall Feb. 15, 1933 2,326,270 Werntz Aug. 10, 1943 FOREIGN PATENTS Number Country Date 343,872 Great Britain Feb. 9, 1931 

